Thiocyano ether alcohols



- Patented Apr. 1945 UNITED s'nmazs PATENT osnca I 2,312,800 THIOCYANO ETHEB ALCOEOIS- Herman A. Brnson, Philadelphia, Pa., assignor to & Haas Company, corporation of Delaware No 1mm. Application men 14, 1944,

I SerlqlN I This invention relates to thiocyano .hols having the formula: T

wherein R is halogen and X is hydrogen or methpolyalkylene ether haloyl and n is an integer from 1 to 3, inclusive, re-' act smoothly with salts of thiocyanic acid to yield the thioc'yano ether alcohols of the present inether alcowherein X is hydrogen or methyl and a is a small momma mums. (onto-45s) Example 2 A mixture consisting of equlmolecular quanti ties of potassium thiocyanate anddipropylene glycol chlorhydrin,

cwmcH-n-cm-cmon CH: H:

, was boiled the presence-of twice itsweisht of water for five hours' under reflux. The product was evaporated to dryness, extracted with acetone, and the acetone extract evaporated to dryness.

cyanoisopropoxy isopropanol, on; cm

arcs-drn-cm-o-tm-cmon Example 3 A mixture consisting of 100 grams of sodium thiocyanate, 160 grams of triethylene glycol chlorhydrin,

c1cmcm-o-cmcm-o-cmcmon and 200 grams of water was boiled under reflux for live hours. The water was then evaporated oil under reduced pressure and the residue exvention without the formation of undesirablecyclic bodies.

The reaction canzbe carried out in water or in an inert solvent, such as acetone, alcohol, tolu- I ene, or methyl isobutyl ketone, at temperatures from about 50 to 150 C. Typical salts of thiocyanic acid-which can be used are, for example, sodium, potassium, calcium, lead, or ammonium thiocyanates. v

The following examples illustrate this invention:

Example 1 A mixture consisting of 188 grams of pchloroethoxyethanol,

clcmcm-o-cmcmoa 121 grams of pure sodium thiocyanate, and 100 gramsof water was stirred and boiled under refluxfor three hours. The product was cooled and the salt filtered oil by suction. The salt was washed with ethylene dichloride and the washings combined with the filtrate, which ,was evaporated to dryness under reduced pressureby being heated on a steam bath. The residual oil (230 grams) was filtered from a trace of salt and distilled in vacuo to yield l50grams of p-thiocy- 'anoethcxyethanol,

tracted with was then evaporated to ethylene dichloride. The extract dryness and the oil 131- tered free from traces of salt.

t It is readily soluble in water.

- The oily product consisted essentially of pthiocyanoethoxyethoxy tanol,

NOS-CHzQHfiO-CH CHr-O-CHzCHsOH In a similar manner, tetraethylene glycol chlorhydrln yields the corresponding NOBCHgCHr-O-CHzCHr-O-CHgCHi-O-CHzCHaOH as a colorless oil.

I claim: 1. As a new compound, a'thi'ocyano ether alcohol having the formula:

wherein X is a member of the groupconsisting'of hydrogen and methyl and n is a small integer from 1 to 3, inclusive.

as acolorless oil boiling at lav-142" c. at 2 mm.

Upon redistillatlon', the compound boiled at 104- 105' C./0.5 mm. and possessed theechstants: a 1.4065; d1 1,1856.

' 2. As a new compound, p-thiocyanoethoxyethano l, V

ncs-crncm-o-cmcmon 3. 'As a new compound, p-thiocyanoethoxyeth' oxyethanol,

ads-mmcrL-o-cmom-o-omcmon 4. As anew compound, p-th'iocyano-isopropoxyisopropanol.

cm cm NcscmcH-ocn--om0n HERMAN A. BRUBON.

The residual oil consisted essentially of p-thiov 

